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Phenylacetaldehyde is an organic compound used in the synthesis of fragrances and polymers. [1] Phenylacetaldehyde is an aldehyde that consists of acetaldehyde bearing a phenyl substituent; the parent member of the phenylacetaldehyde class of compounds.
Phenylglyoxal was first prepared by thermal decomposition of the sulfite derivative of the oxime: [5]. C 6 H 5 C(O)CH(NOSO 2 H) + 2 H 2 O → C 6 H 5 C(O)CHO + NH 4 HSO 4. More conveniently, it can be prepared from methyl benzoate by reaction with KCH 2 S(O)CH 3 to give PhC(O)CH(SCH 3)(OH), which is oxidized with copper(II) acetate. [6]
A much more convenient method for the synthesis of β-phenethylamine is the reduction of ω-nitrostyrene by lithium aluminium hydride in ether, whose successful execution was first reported by R. F. Nystrom and W. G. Brown in 1948. [23] Phenethylamine can also be produced via the cathodic reduction of benzyl cyanide in a divided cell. [24]
[3] [4] In both species, it is subsequently metabolized into 4-hydroxyphenylacetate by aldehyde dehydrogenase (ALDH) enzymes in humans and the phenylacetaldehyde dehydrogenase (feaB) enzyme in E. coli. [3] [4] [5] The condensation of 4-hydroxyphenylacetaldehyde and dopamine is a key step in the biosynthesis of benzylisoquinoline alkaloids.
These compounds are important in the synthesis of heterocyclic compounds. The analogous 1,4-addition of an aldehyde to an enone is called the Stetter reaction . In biochemistry , the coenzyme thiamine is responsible for biosynthesis of acyloin-like compounds utilizing the benzoin addition.
In organic chemistry, a cyanohydrin reaction is an organic reaction in which an aldehyde (−CH=O) or ketone (>C=O) reacts with a cyanide anion (N≡C −) or a nitrile (−C≡N) to form a cyanohydrin (>C(OH)C≡N).
[4] [5] The reaction has since been extended to the synthesis of β-keto esters from the condensation between aldehydes and diazo esters. [6] The general reaction scheme is as follows: General Scheme for Buchner Reaction. The reaction yields two possible carbonyl compounds (I and II) along with an epoxide (III). The ratio of the products is ...
In enzymology, a phenylacetaldehyde dehydrogenase (EC 1.2.1.39) is an enzyme that catalyzes the chemical reaction. phenylacetaldehyde + NAD + + H 2 O phenylacetate + NADH + 2 H +. The 3 substrates of this enzyme are phenylacetaldehyde, NAD +, and H 2 O, whereas its 3 products are phenylacetate, NADH, and H +.